Rh-Catalyzed and Self-Directed Aromatic C–H Activation of Enaminones to Divergent Alkenylated and Annulated Compounds

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 27, 2025

By means of simple Rh catalysis, the direct activation ortho-C-H bond in aryl enaminones has been realized with enaminone structure as a traceless directing fragment. The products resulting from C-H alkenylation and further annulation via intramolecular addition could be accessed depending upon alkenes. annulated used for easy synthesis valuable 2-aza-fluorenones one-pot operation by employing NH4OAc.

Язык: Английский

---

Accessing 7,8-Dihydroquinoline-2,5-diones via Rh-Catalyzed Olefinic C–H Activation/[4+2] Cyclization

Organic Letters, Год журнала: 2024, Номер 26(24), С. 5136 - 5140

Опубликована: Июнь 7, 2024

Herein, we report a rhodium-catalyzed C–H activation/[4+2] cyclization reaction between α,β-unsaturated amides and iodonium ylides for the synthesis of novel 7,8-dihydroquinoline-2,5-diones analogues. This protocol provides series pyridones fused with saturated cycles good functional group compatibility, water air tolerance, to excellent yields under mild green conditions. Additionally, scale-up can be smoothly performed as low 0.25 mol % catalyst loading. Recycling experiments different transformation were also carried out demonstrate potential synthetic utility this protocol.

Язык: Английский

---

Application of Sulfoxonium Ylides or Iodonium Ylides in Rhodium‐Catalyzed Synthesis of Phenanthrenes

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(8), С. 1744 - 1750

Опубликована: Фев. 22, 2024

Abstract The transmetalation triggered rhodium‐catalyzed C−H bond activation and tandem annulation of 2‐biphenylboronic acids with sulfoxonium ylides or iodonium has been developed. Various products phenanthrenes were constructed under redox‐neutral conditions in 34–86% yields. Several mechanism exploration experiments derivatization reactions conducted sequence to gain a deeper understanding the process potential this transformation. It offers an alternative approach for synthesis phenanthrene derivatives.

Язык: Английский

---

Denitrogenative transformations of aryl-fused 1,2,3-triazoles

Advances in heterocyclic chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

---

Iridium(III)-Catalyzed Cyclization of Oximes with Iodonium Ylides: Synthesis of Multisubstituted Heterocyclic N-Oxides

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 29, 2025

Iridium(III)-catalyzed regioselective cyclization of substituted oximes with iodonium ylides has been described. This methodology offered multisubstituted heterocyclic N-oxides under mild reaction conditions in a redox-neutral manner. The was also compatible vinyl oximes. Additionally, substrate diversification carried out to illustrate the synthetic application protocol. A possible mechanism involving C-H bond activation proposed as well supported by isolation key five-membered iridacycle intermediate.

Язык: Английский

---

Advances in Metal-Catalyzed Denitrogenative Pathways for N-Heterocycle Synthesis

Topics in Catalysis, Год журнала: 2023, Номер 67(1-4), С. 246 - 262

Опубликована: Окт. 24, 2023

Язык: Английский

---

Transition-Metal-Catalyzed Directed C–H Bond Functionalization with Iodonium Ylides: A Review of the Last 5 Years

Molecules, Год журнала: 2024, Номер 29(15), С. 3567 - 3567

Опубликована: Июль 29, 2024

Transition-metal-catalyzed directed C-H functionalization with various carbene precursors has been widely employed for constructing a wide range of complex and diverse active molecules through metal migratory insertion processes. Among precursors, iodonium ylides serve as novel emerging precursor features including easy accessibility, thermal stability high activity, which have attracted great attention from organic chemists achieved tremendous success in transformation. In this review, recent progress on the application multifunctional coupling characteristics bond activation reactions is summarized, potential discussed.

Язык: Английский

---

Synthesis of 1H-Isochromenes via Iridium-Catalyzed Cascade C–H Activation/Annulation of Pyridotriazoles at Room Temperature

Organometallics, Год журнала: 2023, Номер 42(16), С. 2228 - 2237

Опубликована: Авг. 7, 2023

An efficient iridium-catalyzed C–H activation/annulation reaction utilizing pyridotriazole as the traceless bifunctional directing group and carbene precursor to form 1H-isochromenes was described. This proceeded smoothly under an additive-free condition at room temperature, which is compatible with a wide range of functional groups in high yields.

Язык: Английский

---

Access to Amides and Lactams via Pyridotriazole as a Transformable Directing Group

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(22), С. 15597 - 15607

Опубликована: Ноя. 2, 2023

Amide and lactam frameworks were synthesized via an efficient two-step strategy. In this protocol, pyridotriazoles first treated with isocyanates to form the corresponding amides, which found be sufficiently reactive undergo subsequent intramolecular N-H insertion in absence of any additional reagents or catalysts.

Язык: Английский

---

Rhodium‐Catalyzed Regioselective C—O and C—C Bonds Formation of 3‐Oxopent‐4‐enenitriles with Alkynes for the Synthesis of Polysubstituted 2H‐Pyrans

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(17), С. 1986 - 1992

Опубликована: Апрель 25, 2024

Comprehensive Summary The rhodium‐catalyzed C—H bond activation and cyclization of 3‐oxopent‐4‐enenitriles with alkynes proceed efficiently. Various 2 H ‐pyrans multiple substituents are achieved in good yields through regioselective formation C—O C—C bonds. Transformations involving hydroxy‐alkynoates resulted products a furo[3,4‐ b ]pyran skeleton via further intramolecular ester exchange processes. Different from the traditional “1‐oxatrienes pathway”, this method for synthesis useful possesses certain highlights terms readily available substrates, stable easily derivatized products, gentle convenient operation process, step atom economy.

Язык: Английский

---